1360446-87-2

Upstream product

• 1345545-23-4 (E)-6-(3,7-dimethylocta-2,6-dienyl)-5-methoxy-7-(methoxymethoxy)isobenzofuran-1(3H)-one 
• 1345545-24-5 C₂₁H₃₂O₅ 
• 1381789-16-7 (E)-4-(3,7-dimethylocta-2,6-dienyl)-2-(hydroxymethyl)-5-methoxy-3-(methoxymethoxy)-N-phenethylbenzamide 
• 1381789-17-8 (E)-2-(chloromethyl)-4-(3,7-dimethylocta-2,6-dienyl)-5-methoxy-3-(methoxymethoxy)-N-phenethylbenzamide 
• 1381789-18-9 (E)-5-(3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one 
• 1381789-15-6 (E)-5-(3,7-dimethylocta-2,6-dienyl)-6-methoxy-4-(methoxymethoxy)isobenzofuran-1(3H)-one 
• 1426175-75-8 C₂₀H₂₈O₄ 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 59384-87-1 (E)-2-(3,7-dimethylocta-2,6-dienyloxy)-4-methoxybenzaldehyde 
• 1426175-70-3 (E)-3-(3,7-dimethylocta-2,6-dienyl)-2-hydroxy-4-methoxybenzaldehyde 
• 6138-90-5 trans-geranyl bromide 

Relevant academic research and scientific papers

A concise total synthesis and PPAR activation activity of hericerin from Hericium erinaceum

Hericerin is an isoindolinone meroterpenoid alkaloid isolated from medicinal mushroom Hericium erinaceum with some bioactivities. Herein, a concise total synthesis of hericerin was described, with four steps and 30percent overall yield starting from commercially available methyl 3-hydroxy-5-methoxybenzoate and geranyl bromide. A comprehensive effect of hericerin on HepG2 cell line was observed and confirmed by transcriptomic analysis. Furthermore, hericerin was found to be a new PPARγ agonist.

De novo Assembly of the Benzenoid Ring as a Core Strategy for Synthesis of the Isoindolinone Natural Products Isohericerin, Erinacerin A, and Sterenin A

Here we describe the use of the hexadehydro-Diels-Alder (HDDA) reaction for the de novo construction of the isoindolinone scaffold and its application to the synthesis of the title natural products. The key isoindolinone-forming HDDA reaction involved an unprecedented substrate motif in which an amide carbonyl group was conjugated to the 4π1,3-diyne component. In addition, a dimethylsilyl (-SiMe2H) substituent was exploited to trigger a Fleming-Tamao-Kumada oxidation for the installation of an essential phenolic hydroxyl group.

Total Synthesis of Isohericerin, Isohericenone, and Erinacerin A: Development of a Copper-Catalyzed Methylboronation of Terminal Alkynes

Efficient and concise approaches for the synthesis of three bioactive natural products, isohericerin, isohericenone, and erinacerin A, are described in this paper. The key reactions employed include a Mannich reaction with commercially available hydroxybenzoate and subsequent one-pot lactamization to afford the common precursor isoindolinone in 3 steps and a Suzuki-Miyaura coupling reaction to connect geranyl side chains to the isoindolinone core. In addition, the mild and efficient synthesis of the C5′-oxidized geranyl side unit of isohericenone is enabled by developing a highly regioselective and efficient method for the Cu-catalyzed methylboronation of functionalized terminal alkynes.

Concise total synthesis of hericerin natural product

A concise total synthesis of hericerin, a natural product, is described. The all-synthetic sequence comprises five steps and was accomplished in 34% overall yield starting from commercially available 2-hydroxy-4- methoxybenzaldehyde. The key steps were the introduction of the geranyl group using a ether-phenol rearrangement and the formation of isoindolinone through a Pd(OAc)2-catalyzed carbonylative ring closure.

Total synthesis and structural revision of hericerin

The total synthesis of hericerin, a pollen growth inhibitor from Hericium erinaceum, was achieved. We found that the reported structure of hericerin should be revised to be the carbonyl regioisomer.